108268-28-6

Basic information

• Product Name: (R,R)-(-)-1,2-CYCLOHEPTANEDIOL
• Synonyms: (R,R)-(-)-1,2-CYCLOHEPTANEDIOL
• CAS NO: 108268-28-6
• Molecular Formula: C₇H₁₄O₂
• Molecular Weight: 130.18
• Mol File: 108268-28-6.mol
• Article Data: 43

Chemical Properties

• Boiling Point: 248.9±8.0 °C(Predicted)
• Appearance: /
• Density: 1.101±0.06 g/cm3(Predicted)
• PKA: 14.51±0.40(Predicted)
• CAS DataBase Reference: (R,R)-(-)-1,2-CYCLOHEPTANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-(-)-1,2-CYCLOHEPTANEDIOL(108268-28-6)
• EPA Substance Registry System: (R,R)-(-)-1,2-CYCLOHEPTANEDIOL(108268-28-6)

Safety Data

• Hazardous Substances Data: 108268-28-6(Hazardous Substances Data)

Usage

General Description

(R,R)-(-)-1,2-CYCLOHEPTANEDIOL is a chemical compound with the molecular formula C7H14O2. It is a colorless, viscous liquid and is commonly used as a chiral building block in organic synthesis. (R,R)-(-)-1,2-CYCLOHEPTANEDIOL has two stereocenters, resulting in a pair of enantiomers, with the (R,R) enantiomer being the most commonly used form. (R,R)-(-)-1,2-CYCLOHEPTANEDIOL is often employed in the synthesis of pharmaceuticals and fine chemicals due to its ability to impart chirality and influence the stereochemical outcome of various reactions. It is also used in the production of perfumes and fragrances, as well as in the development of new materials and compounds in the field of organic chemistry.

Upstream product

• 628-92-2 Cycloheptene 
• 100-49-2 cyclohexylmethyl alcohol 
• 291-64-5 cycloheptane 
• 7553-56-2 iodine 
• 563-63-3 silver(I) acetate 
• 3603-86-9 trans-cycloheptane-1,2-dicarboxylic acid 
• 99181-53-0 (+/-)-trans-2-acetyl-cycloheptanecarboxylic acid 
• 13553-19-0 trans-cycloheptane-1,2-diol 
• 97-72-3 2-Methylpropionic anhydride 
• 76519-87-4 (1R,7S)-cycloheptene oxide 
• 108-24-7 acetic anhydride 
• 78823-36-6 p-nitrobenzoic-propionic anhydride 
• 51075-28-6 2-bromo-3-phenylpropanal 
• 286-45-3 8-oxabicyclo[5.1.0]octane 

Downstream Products

• 111-16-0 heptanedioic acid 
• 145264-93-3 2-((1S,5S,6S)-3-Phenyl-bicyclo[3.2.1]oct-3-en-6-yl)-ethanol 
• 145222-77-1 2-((1R,5R,6R)-3-Phenyl-bicyclo[3.2.1]oct-3-en-6-yl)-ethanol 
• 145222-73-7 ((1S,5S,6S)-3-Phenyl-bicyclo[3.2.1]oct-3-en-6-yl)-acetic acid (1R,2R)-2-hydroxy-cycloheptyl ester 
• 145222-73-7 ((1R,5R,6R)-3-Phenyl-bicyclo[3.2.1]oct-3-en-6-yl)-acetic acid (1R,2R)-2-hydroxy-cycloheptyl ester 
• 145511-67-7 2-((1S,5S,6S)-3-Cyclohexyl-bicyclo[3.2.1]oct-3-en-6-yl)-ethanol 
• 145222-76-0 2-((1R,5R,6R)-3-Cyclohexyl-bicyclo[3.2.1]oct-3-en-6-yl)-ethanol 
• 145222-71-5 ((1S,5S,6S)-3-Cyclohexyl-bicyclo[3.2.1]oct-3-en-6-yl)-acetic acid (1R,2R)-2-hydroxy-cycloheptyl ester 
• 145222-71-5 ((1R,5R,6R)-3-Cyclohexyl-bicyclo[3.2.1]oct-3-en-6-yl)-acetic acid (1R,2R)-2-hydroxy-cycloheptyl ester 
• 53185-69-6 pimelaldehyde 
• 251979-90-5 cis-1,2-diaminocycloheptane 
• 1373965-43-5 2-methoxy-6,7,8,9-tetrahydro-5H-10-oxabenzo[a]azulene 

Relevant articles and documents

Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of trans to cis Diols

Traditional approaches to stereoselective synthesis require high levels of enantio- and diastereocontrol in every step that forms a new stereocenter. Here, we report an alternative approach, in which the stereochemistry of organic substrates is selectivel

Absolute configuration of trans-perhydroazulene

We present the absolute configuration (AC) determination of an alkane, trans-perhydroazulene (1), that displays the naturally very common trans fused [5,7] ring system. We outline the first synthesis yielding enantiopure 1 and the application of optical rotatory dispersion (ORD) and vibrational circular dichroism (VCD) techniques. The spectroscopic results are in excellent agreement with the computed ORD at B3LYP/6-311++G(2d,2p) and the computed VCD spectrum at B3LYP/6-311++G(d,p), providing an assignment of the AC as (R,R)-(+)-1.

Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts

An extremely efficient acylative kinetic resolution of d,l-1,2-diols in the presence of only 0.5 mol% of binaphthyl-based chiral N,N-4-dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert-alcohol unit(s) of the catalyst and the 1,2-diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2-diols with high selectivity factors. The kinetic resolution of d,l-hydrobenzoin and trans-1,2-cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 °C); (iii) high substrate concentration (1.0 M); and (iv) short reaction time (30 min). (Figure presented.).